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Partial Syntheses of - and -Gibberellin A29 and Gibberellin A51 from Gibberellin A3

DOI: 10.1039/P19810000394

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 394 - 400 (1981)

Update date:2022-08-03

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Authors:

Beale, Michael H.Beale, Michael H.

MacMillan, JakeMacMillan, Jake

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Article abstract of DOI:10.1039/P19810000394

In the partial syntheses of the title compounds gibberellin A3 (GA3) is ozonised to the norketone and the methyl ester (12) is chlorinated with lithium chloride and toluene-p-sulphonyl chloride to give the 3α-chloro-13-alcohol (15) and its 13-toluene-p-sulphonate (14).The 13-alcohol (15) is converted, by tri-n-butylstannane reduction, then reaction with acetyl hypobromite, and reduction with thi-n-butylstannane, into the 2α-acetoxy-16-ketone (23).This intermediate (23) is converted successively into the 16-ene (24), the 2α-alcohol (25), the 2-ketone (26), <2α-2H>- and <2α-3H>-GA29 methyl esters (29) and (31), and finally into <2α-2H>- and <2α-3H>-GA29 (30) and (32).An attempt to convert the 3α-chloro-13-toluene-p-sulphonate (14) into GA29 by analogous reactions was abandoned since tri-n-butylstannane reduction of the 2α-acetoxy-13-toluene-p-sulphonates (18) and (19) resulted in extensive loss of the 13-toluene-p-sulphonyloxy-group.However the resultant 13-deoxy-compound (22) was converted into <2α-2H,15,17-3H2>GA51 (37) as for the 13-alcohol (15).

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Product name:ent-2β-acetoxy-10β-hydroxy-7-methoxycarbonyl-16-oxo-17,20-bisnorgibberellan-19-oic acid 19,10-lactone

Cas No:60346-15-8

60346-15-8

R&D Labs maybe for 60346-15-8

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